Thioxanthene dioxide based amino-protecting groups sensitive to pyridine bases and dipolar aprotic solvents

LA Carpino, HS Gao, GS Ti…

Index: Carpino, Louis A.; Gao, Heau-Shan; Ti, Gen-Shing; Segev, David Journal of Organic Chemistry, 1989 , vol. 54, # 25 p. 5887 - 5897

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Citation Number: 11

Abstract

In pursuit of an analogy between fluorine and thioxanthene dioxide, the suitability of the D- TMOC and related functions as base-sensitive amino-protecting groups was examined. Such compounds were found to be cleaved by mild pyridine bases against which the analogous FMOC derivatives are stable. Deblocking gives as a byprodud the methylene sulfone 5 or its adducts with an appropriate secondary deblocking amine. Certain solvents ...